$138-$301 — Chicago to Orlando & Key West (R/T)

Summer flights to Orlando and Key West are now $100 off the next lowest fare. If you’ve been thinking about visiting Key West, grab this fare, as Key West is always expensive, so this great price drop!

Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!